How long is the flight from Kentucky to Chicago?

There are many flights that can get you from Kentucky to Chicago in 1h 32m. Fly via United Airlines, Southwest, or Allegiant Air to get the fastest option. The distance from Kentucky to Chicago is about 460 mi. Most flights are nonstop.

What are the cheapest airlines to fly from Kentucky to Chicago one-way?

To fly one-way, consider booking your trip with Spirit Airlines, which is currently one of the cheapest options available, starting at $50. United Airlines flights start at $51 while deals on Allegiant Air start at $51 one-way.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

What are the most popular routes from Kentucky to Chicago?

The most popular flight routes from Kentucky to Chicago are Cincinnati Cinci./N. Kentucky - Chicago O'Hare Intl, Nashville Intl - Chicago O'Hare Intl and Knoxville McGhee Tyson - Chicago O'Hare Intl.

What are the cheapest flights from Kentucky to Chicago?

On average you can expect to pay $957 for a flight from Kentucky to Chicago. The cheapest flight overall is $75 while the most popular route, (Cincinnati Cinci./N. Kentucky - Chicago O'Hare Intl) is currently priced at $101.

What are the most reliable airlines from Kentucky to Chicago?

Before booking your flight to Chicago from Kentucky, check out the most reliable airlines to get you to your destination on time: Qatar Airways (92%), Republic Airways (91%), Royal Jordanian( 91%).

How far in advance should I book a flight from Kentucky to Chicago?

Users have found that booking a flight from Kentucky to Chicago at least 42 days early can save you up to 282% on average compared to booking a flight this week. If booking 42 days before your flight isn’t an option for you, users have found flights from Kentucky to Chicago for as little as $355 when booking for a departure date within the next two weeks. You can also check prices now. Some users have found airline tickets as low as $472 for flights departing within the next 3 days.

What is the cheapest month to fly from Kentucky to Chicago?

April is one of the best times of the year to fly to Chicago from Kentucky. Prices for April average $260 per person but you can even find prices for as low as $124. The most expensive prices can be found in the month of March. Opting for a April flight can save you 10% on your journey compared to booking in March

Can I find deals for flights from Kentucky to Chicago that include hotel bookings?

Yes. In addition to deals on Kentucky to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

How can I find direct flights from Kentucky to Chicago?

After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Kentucky to Chicago.

Can I find deals for business class flights from Kentucky to Chicago?

Yes. Cheapflights offers flight deals from Kentucky to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

$50+ Flights from Kentucky to Chicago

Q: How much does it cost to fly round-trip from Kentucky to Chicago?

Airfare is below average for this route at the moment. Kentucky to Chicago flights typically cost between $151 and $287 in October. The cheapest round-trip price found within the last 3 days was $101 on United Airlines (Oct 4-Oct 7).

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Cheap flight deals from Kentucky to Chicago

Round-trip from	$80 (Cheapflightsfares)
One-way from	$50 (Orbitz)
Popular in	March
Cheapest in	April
Average price	$245
Good round-trip deal	$138 or less
Good one-way deal	$100 or less

From Kentucky to Chicago (CHI)

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One-way flight from Kentucky to Chicago (CHI)

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High demand for flights, 2% potential price rise

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Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).

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Average for round-trip flights in September 2025

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Price to beat on a round-trip flight from Kentucky to Chicago (CHI).

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Price to beat on a one-way flight from Kentucky to Chicago (CHI).

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Find flight deals from Kentucky to Chicago

Cheapest flights from Kentucky to Chicago
Explore the most affordable flight options available from Kentucky to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

Fri 10/172:01 pmBNA - ORD

Nonstop1h 48mSpirit Airlines

Sun 10/191:26 pmORD - BNA

Nonstop1h 44mSpirit Airlines

Deal found 9/10

$80

Thu 10/233:24 pmBNA - ORD

Nonstop1h 55mFrontier

Mon 10/277:25 pmORD - BNA

Nonstop1h 44mFrontier

Deal found 9/9

$82

Thu 10/212:48 pmBNA - ORD

Nonstop2h 00mFrontier

Fri 10/312:31 pmORD - BNA

Nonstop1h 43mFrontier

Deal found 9/10

$84

Thu 10/93:24 pmBNA - ORD

Nonstop1h 55mMultiple Airlines

Thu 10/161:26 pmORD - BNA

Nonstop1h 44mMultiple Airlines

Deal found 9/11

$86

Thu 10/212:48 pmBNA - ORD

Nonstop2h 00mFrontier

Sun 10/512:43 pmORD - BNA

Nonstop1h 43mFrontier

Deal found 9/11

$88

Sun 11/29:02 pmBNA - ORD

Nonstop1h 47mSpirit Airlines

Thu 11/64:01 pmORD - BNA

Nonstop1h 40mSpirit Airlines

Deal found 9/10

$90

Mon 10/139:59 pmBNA - ORD

Nonstop1h 45mMultiple Airlines

Thu 10/161:26 pmORD - BNA

Nonstop1h 44mMultiple Airlines

Deal found 9/10

$91

Thu 10/93:24 pmBNA - ORD

Nonstop1h 55mFrontier

Sun 10/1212:41 pmORD - BNA

Nonstop1h 36mFrontier

Deal found 9/9

$93

Fri 10/1710:44 amTYS - MDW

Nonstop1h 32mAllegiant Air

Mon 10/2012:08 pmMDW - TYS

Nonstop1h 24mAllegiant Air

Deal found 9/11

$96

Sat 11/13:42 pmBNA - ORD

1 stop8h 30mFrontier

Sun 11/26:06 pmORD - BNA

Nonstop1h 48mFrontier

Deal found 9/10

$100

Sat 10/45:48 pmSDF - ORD

Nonstop1h 47mUnited Airlines

Tue 10/72:42 pmORD - SDF

Nonstop1h 31mUnited Airlines

Deal found 9/10

$101

Wed 10/19:10 amBNA - MDW

Nonstop1h 35mSouthwest

Tue 10/78:20 pmMDW - BNA

Nonstop1h 25mSouthwest

Deal found 9/10

$101

Best flights from Kentucky to Chicago
Discover carefully curated flight deals from Kentucky to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 11, 2025.

Wed 11/59:00 amSDF - ORD

Nonstop1h 40mUnited Airlines

Tue 11/187:55 pmORD - SDF

Nonstop1h 34mUnited Airlines

Deal found 9/10

$101

Wed 10/19:10 amBNA - MDW

Nonstop1h 35mSouthwest

Tue 10/74:10 pmMDW - BNA

1 stop3h 55mSouthwest

Deal found 9/10

$111

Fri 10/241:23 pmTYS - MDW

Nonstop1h 32mAllegiant Air

Fri 10/317:06 pmMDW - TYS

Nonstop1h 24mAllegiant Air

Deal found 9/9

$117

Fri 10/177:02 pmTYS - MDW

1 stop23h 11mMultiple Airlines

Mon 10/2012:08 pmMDW - TYS

Nonstop1h 24mMultiple Airlines

Deal found 9/10

$154

Wed 11/510:30 amSDF - ORD

1 stop6h 41mDelta

Tue 11/189:46 amORD - SDF

1 stop6h 30mDelta

Deal found 9/10

$177

Sat 11/1511:09 amCVG - ORD

1 stop5h 28mAmerican Airlines

Wed 11/1911:50 amORD - CVG

Nonstop1h 21mAmerican Airlines

Deal found 9/11

$178

Tue 10/218:50 pmBNA - MDW

Nonstop1h 35mSouthwest

Wed 10/223:00 pmMDW - BNA

1 stop3h 55mSouthwest

Deal found 9/9

$111

Tue 10/289:00 amSDF - ORD

Nonstop1h 40mUnited Airlines

Thu 10/307:55 pmORD - SDF

Nonstop1h 34mUnited Airlines

Deal found 9/9

$117

Tue 9/3011:10 amBNA - ORD

1 stop6h 45mSouthwest

Wed 10/13:10 pmORD - BNA

Nonstop1h 35mSouthwest

Deal found 9/9

$111

Sat 10/119:51 amBNA - ORD

Nonstop1h 54mUnited Airlines

Mon 10/137:15 amORD - BNA

Nonstop1h 40mUnited Airlines

Deal found 9/11

$117

Wed 10/151:50 pmBNA - MDW

1 stop3h 15mSouthwest

Sat 10/1812:55 pmMDW - BNA

1 stop5h 25mSouthwest

Deal found 9/11

$116

Sat 11/18:00 amBNA - ORD

Nonstop1h 50mUnited Airlines

Mon 11/33:45 pmORD - BNA

Nonstop1h 44mUnited Airlines

Deal found 9/10

$117

Last-minute flights from Kentucky to Chicago
Discover last-minute flight deals from Kentucky to Chicago. Data last updated September 11, 2025 and is based on user searches.

Wed 10/19:10 amBNA - MDW

Nonstop1h 35mSouthwest

Tue 10/78:20 pmMDW - BNA

Nonstop1h 25mSouthwest

Deal found 9/10

$101

Thu 10/212:48 pmBNA - ORD

Nonstop2h 00mFrontier

Fri 10/312:31 pmORD - BNA

Nonstop1h 43mFrontier

Deal found 9/10

$84

Thu 10/212:48 pmBNA - ORD

Nonstop2h 00mFrontier

Sun 10/512:43 pmORD - BNA

Nonstop1h 43mFrontier

Deal found 9/11

$88

Sat 10/45:48 pmSDF - ORD

Nonstop1h 47mUnited Airlines

Tue 10/72:42 pmORD - SDF

Nonstop1h 31mUnited Airlines

Deal found 9/10

$101

Wed 10/89:51 amBNA - ORD

Nonstop1h 54mUnited Airlines

Wed 10/1510:55 amORD - BNA

Nonstop1h 40mUnited Airlines

Deal found 9/10

$101

Thu 10/93:24 pmBNA - ORD

Nonstop1h 55mMultiple Airlines

Thu 10/161:26 pmORD - BNA

Nonstop1h 44mMultiple Airlines

Deal found 9/11

$86

Thu 10/99:02 pmBNA - ORD

Nonstop1h 47mSpirit Airlines

Thu 10/161:26 pmORD - BNA

Nonstop1h 44mSpirit Airlines

Deal found 9/11

$90

Mon 10/139:59 pmBNA - ORD

Nonstop1h 45mMultiple Airlines

Thu 10/161:26 pmORD - BNA

Nonstop1h 44mMultiple Airlines

Deal found 9/10

$91

Fri 10/172:01 pmBNA - ORD

Nonstop1h 48mSpirit Airlines

Sun 10/191:26 pmORD - BNA

Nonstop1h 44mSpirit Airlines

Deal found 9/10

$80

Fri 10/1710:44 amTYS - MDW

Nonstop1h 32mAllegiant Air

Mon 10/2012:08 pmMDW - TYS

Nonstop1h 24mAllegiant Air

Deal found 9/11

$96

Thu 10/233:24 pmBNA - ORD

Nonstop1h 55mMultiple Airlines

Fri 10/244:44 pmORD - BNA

Nonstop1h 40mMultiple Airlines

Deal found 9/11

$89

Sun 10/269:02 pmBNA - ORD

Nonstop1h 47mMultiple Airlines

Mon 10/277:25 pmORD - BNA

Nonstop1h 44mMultiple Airlines

Deal found 9/11

$99

One-way flights from Kentucky to Chicago
Search for one-way flight options from Kentucky to Chicago. Find affordable one-way fares based on user searches. Data last updated September 11, 2025.

Sun 11/29:02 pmBNA - ORD

Nonstop1h 47mSpirit Airlines

Deal found 9/10

$50

Tue 12/912:20 pmSDF - ORD

Nonstop1h 38mUnited Airlines

Deal found 9/11

$51

Sat 10/114:25 pmSDF - MDW

Nonstop1h 15mSouthwest

Deal found 9/11

$51

Fri 11/142:02 pmTYS - MDW

Nonstop1h 35mAllegiant Air

Deal found 9/10

$51

Sat 11/85:40 amBNA - MDW

Nonstop1h 40mSouthwest

Deal found 9/10

$51

Sat 11/812:10 pmBNA - ORD

Nonstop1h 50mUnited Airlines

Deal found 9/10

$51

Tue 10/286:35 amCVG - MDW

Nonstop1h 10mSouthwest

Deal found 9/10

$51

Wed 10/158:45 amCVG - ORD

Nonstop1h 26mUnited Airlines

Deal found 9/10

$51

Wed 11/127:39 amSDF - ORD

Nonstop1h 40mAmerican Airlines

Deal found 9/11

$52

Sun 11/96:46 pmBNA - ORD

Nonstop1h 45mSpirit Airlines

Deal found 9/11

$55

Wed 10/151:50 pmBNA - MDW

1 stop3h 15mSouthwest

Deal found 9/10

$56

Fri 11/71:32 pmTYS - MDW

Nonstop1h 35mAllegiant Air

Deal found 9/9

$58

Fly from

Fly to

Route

Depart

Return

Price

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

Wed 11/5

9:00 am-9:40 am

Nonstop1h 40m

Chicago O'Hare Intl

Tue 11/18

7:55 pm-10:29 pm

Nonstop1h 34m

$101

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Wed 10/1

9:10 am-10:45 am

Nonstop1h 35m

Chicago Midway

Tue 10/7

4:10 pm-8:05 pm

1 stop3h 55m

$111

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Tue 10/21

8:50 pm-10:25 pm

Nonstop1h 35m

Chicago Midway

Wed 10/22

3:00 pm-6:55 pm

1 stop3h 55m

$111

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Tue 9/30

11:10 am-5:55 pm

1 stop6h 45m

Chicago O'Hare Intl

Wed 10/1

3:10 pm-4:45 pm

Nonstop1h 35m

$111

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Wed 10/15

1:50 pm-5:05 pm

1 stop3h 15m

Chicago Midway

Sat 10/18

12:55 pm-6:20 pm

1 stop5h 25m

$116

KnoxvilleChicago

TYS - MDW

TYSMDW

Knoxville McGhee Tyson

Fri 10/24

1:23 pm-1:55 pm

Nonstop1h 32m

Chicago Midway

Fri 10/31

7:06 pm-9:30 pm

Nonstop1h 24m

$117

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

Tue 10/28

9:00 am-9:40 am

Nonstop1h 40m

Chicago O'Hare Intl

Thu 10/30

7:55 pm-10:29 pm

Nonstop1h 34m

$117

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Sat 10/11

9:51 am-11:45 am

Nonstop1h 54m

Chicago O'Hare Intl

Mon 10/13

7:15 am-8:55 am

Nonstop1h 40m

$117

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Sat 11/1

8:00 am-9:50 am

Nonstop1h 50m

Chicago O'Hare Intl

Mon 11/3

3:45 pm-5:29 pm

Nonstop1h 44m

$117

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Tue 10/28

11:55 am-12:10 pm

Nonstop1h 15m

Chicago Midway

Thu 10/30

9:55 am-12:05 pm

Nonstop1h 10m

$117

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

Showing 1-10 of 60 results

...

Best time to book a flight from Kentucky to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Kentucky with our price prediction graph.

Estimated round-trip price

Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Kentucky to Chicago

What is the cheapest month to book a flight from Kentucky to Chicago?

Currently, August is the cheapest month in which you can book a flight from Kentucky to Chicago (average of $245). Flying from Kentucky to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from KY to CHI?

When flying from Kentucky to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Kentucky to Chicago

The most flights from USKY to CHI are scheduled on a Monday (43 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (32 on average).

How much does it cost to fly round-trip from Kentucky to Chicago?

Related info for your journey

How long is the flight from Kentucky to Chicago?
There are many flights that can get you from Kentucky to Chicago in 1h 32m. Fly via United Airlines, Southwest, or Allegiant Air to get the fastest option. The distance from Kentucky to Chicago is about 460 mi. Most flights are nonstop.
What are the cheapest airlines to fly from Kentucky to Chicago one-way?
To fly one-way, consider booking your trip with Spirit Airlines, which is currently one of the cheapest options available, starting at $50. United Airlines flights start at $51 while deals on Allegiant Air start at $51 one-way.
What are the most popular routes from Kentucky to Chicago?
The most popular flight routes from Kentucky to Chicago are Cincinnati Cinci./N. Kentucky - Chicago O'Hare Intl, Nashville Intl - Chicago O'Hare Intl and Knoxville McGhee Tyson - Chicago O'Hare Intl.
What are the most reliable airlines from Kentucky to Chicago?
Before booking your flight to Chicago from Kentucky, check out the most reliable airlines to get you to your destination on time: Qatar Airways (92%), Republic Airways (91%), Royal Jordanian( 91%).
What are the cheapest flights from Kentucky to Chicago?
On average you can expect to pay $957 for a flight from Kentucky to Chicago. The cheapest flight overall is $75 while the most popular route, (Cincinnati Cinci./N. Kentucky - Chicago O'Hare Intl) is currently priced at $101.
Can I find deals for flights from Kentucky to Chicago that include hotel bookings?
Yes. In addition to deals on Kentucky to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Kentucky to Chicago?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Kentucky to Chicago.
Can I find deals for business class flights from Kentucky to Chicago?
Yes. Cheapflights offers flight deals from Kentucky to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.
What is the cheapest month to book a flight from Kentucky to Chicago?
Currently, August is the cheapest month in which you can book a flight from Kentucky to Chicago (average of $245). Flying from Kentucky to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Merrillville

Lansing

Hammond

Benton Harbor

Porter

Chesterton

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Top 4 airlines flying from Kentucky to Chicago

Airline	Cheapest	Average	Flexibility	On-time
American Airlines	Cheapest$97	Average$264	FlexibilityNo cancel fee	On-time71%
Southwest	Cheapest$97	Average$261	FlexibilityNo cancel fee	On-time63%
Contour	Cheapest$113	Average$144	FlexibilityNo cancel fee	On-timeN/A
United Airlines	Cheapest$128	Average$287	FlexibilityNo cancel fee	On-time69%

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$50+ Cheap flights from Kentucky to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/2. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Kentucky to Chicago with Cheapflights

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Cheap flight deals from Kentucky to Chicago

Keep the following information in mind while searching for Kentucky to Chicago flight deals. Data was last updated September 11, 2025.

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Good round-trip deal

Good one-way deal

Find flight deals from Kentucky to Chicago

Cheapest flights from Kentucky to ChicagoExplore the most affordable flight options available from Kentucky to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

Explore the most affordable flight options available from Kentucky to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Kentucky to Chicago that are best for you.

Best time to book a flight from Kentucky to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Kentucky with our price prediction graph.

Cheapflights Insights

Everything you need to know about your flight from Kentucky to Chicago

What is the cheapest month to book a flight from Kentucky to Chicago?

What is the cheapest time of day to fly from KY to CHI?

Find hourly flight availability from Kentucky to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 11, 2025.

Weekly flight availability from Kentucky to Chicago

Explore weekly flight availability from Kentucky to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated September 11, 2025.

How much does it cost to fly round-trip from Kentucky to Chicago?

Related info for your journey

Find useful and relevant information for your journey from Kentucky to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

How long is the flight from Kentucky to Chicago?

What are the cheapest airlines to fly from Kentucky to Chicago one-way?

What are the most popular routes from Kentucky to Chicago?

What are the most reliable airlines from Kentucky to Chicago?

What are the cheapest flights from Kentucky to Chicago?

Can I find deals for flights from Kentucky to Chicago that include hotel bookings?

How can I find direct flights from Kentucky to Chicago?

Can I find deals for business class flights from Kentucky to Chicago?

What is the cheapest month to book a flight from Kentucky to Chicago?

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Alternative routes for Kentucky to Chicago

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Top 4 airlines flying from Kentucky to Chicago

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Cheapest flights from Kentucky to Chicago
Explore the most affordable flight options available from Kentucky to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.